6-[2-(Dimethylamino)ethoxy]pyridin-3-amine → 6-Chloro-N-(6-(2-(dimethylamino)ethoxy)pyridin-3-yl)-3-(methylsulfonyl)-1,5-naphthyridin-4-amine

HRID 526184Notes

Reaction equation

HRID 526184 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5](Cl)[C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][N:8]=2)[N:3]=1.[CH3:17][N:18]([CH3:29])[CH2:19][CH2:20][O:21][C:22]1[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1>>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:28][C:25]1[CH:26]=[N:27][C:22]([O:21][CH2:20][CH2:19][N:18]([CH3:29])[CH3:17])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 206914066-[2-(Dimethylamino)ethoxy]pyridin-3-amineHCID 1177730332,8-Dichloro-7-(methylsulfonyl)-1,5-naphthyridine

Product 1

HCID 1177742206-Chloro-N-(6-(2-(dimethylamino)ethoxy)pyridin-3-yl)-3-(methylsulfonyl)-1,5-naphthyridin-4-amineYield 70.2%

Procedure

Following general procedure I, 2,8-dichloro-7-(methylsulfonyl)-1,5-naphthyridine (150 mg, 0.54 mmol) was reacted with 6-[2-(dimethylamino)ethoxy]pyridin-3-amine (120 mg, 0.65 mmol) to afford the desired product (160 mg, 70%) as a light yellow solid; 1H NMR (500 MHz, CDCl3) δ 9.03 (s, 1H), 8.98 (s, 1H), 8.17 (d, J=8.8 Hz, 1H), 7.98 (d, J=2.8 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.42 (dd, J=8.8, 2.8 Hz, 1H), 6.82 (d, J=8.8 Hz, 1H), 4.46 (t, J=5.5 Hz, 2H), 3.20 (s, 3H), 2.76 (t, J=5.6 Hz, 2H), 2.37 (s, 6H); ESI MS m/z 422 [M+H]+

Sources & evidence

ORD record
ord-cfa5b647fc714b9190a0ea92b2c3ca32
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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